Iodoethane → 2-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine

HRID 9915Notes

Reaction equation

HRID 9915 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([NH:6][CH:7]=[N:8]2)=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[N:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:27][CH3:28].O1CCOCC1>C(OCC)(=O)C.CN(C=O)C.O>[Cl:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[CH2:27][CH3:28])=[C:4]([NH:11][C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]#[N:19])[CH:13]=2)[N:3]=1

Participants

8

Reactant 4

HCID 6340IodoethaneHCID 10796Cesium carbonateHCID 312751,4-DioxaneHCID 21988299HCID 21988299, compound

Product 1

HCID 219882732-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

1.5 g (3.95 mmol) of 2-chloro-6-(3-cyano-phenyl-amino)-purine, 2.1 g (6.3 mmol) of caesium carbonate and 2.6 ml (31.6 mmol) of iodoethane are stirred in 66 ml of a mixture comprising dioxane:water:DMF in a ratio of 1:2:3 at RT for 19 h. Thereafter, the reaction mixture is diluted with ethyl acetate and the organic phase is washed with water. After drying over sodium sulfate, the residue is chromatographed over silica gel (mobile phase: ethyl acetate:hexane=4:1). After removal of the solvent, 2-chloro-9-ethyl-6-(3-cyano-phenyl-amino)-9H-purine is obtained as a crystalline precipitate. This precipitate is filtered off and dried; m.p. 189° C.; FAB-MS: (M+H)+=299; Rf=0.9 (CH2Cl2:methanol 9:1).

Workup

  1. washthe organic phase is washed with water
  2. dry with materialAfter drying over sodium sulfate
  3. customthe residue is chromatographed over silica gel (mobile phase: ethyl acetate:hexane=4:1)
  4. customAfter removal of the solvent

Sources & evidence

ORD record
ord-b125fb03c3bd4ad09878ca15f280ae05
Source dataset
uspto-grants-2006_08
Patent number
US07091346B1

Reaction notes

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